2-(2-nitrophenyl)quinoline | 5278-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-nitrophenyl)quinoline
• 英文别名: 2-o-Nitrophenylquinoline
• CAS: 5278-56-8
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: OZOVSOGYLNHVML-UHFFFAOYSA-N

物化性质

• 熔点：
  118.5-119.5 °C
• 沸点：
  187-190 °C(Press: 0.2 Torr)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenyl)quinoline 在 氢氧化钾 、 barium(II) oxide 、 亚磷酸三乙酯 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 白叶藤碱
  参考文献：
  名称：

  Thermal cyclization of 3-arylamino-3-(2-nitrophenyl)-propenal Schiff base hydrochlorides followed by triethyl phosphite mediated deoxygenation: a facile synthesis of quindolines

  摘要：

  A simple and useful method for the synthesis of various 2-substituted quindolines starting from 2-nitroacetophenone is described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.007
• 作为产物：
  描述：

  邻硝基苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 2-(2-nitrophenyl)quinoline
  参考文献：
  名称：

  Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

  摘要：

  We have encountered a superbase‐mediated chemoselective reaction of N‐tosylhydrazones with aza‐ortho‐quinone methide precursors. When tosylhydrazone was treated with ortho‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation of 2‐substituted quinoline. The reaction was found to be general, and by this method, mono‐, di‐ and tri‐substituted quinolines could be made. We could prove experimentally and theoretically that the reaction proceeded via the formation of an azine from the basic decomposition of N‐tosylhydrazones. Finally, the reaction of tosylhydrazone with N‐(2‐(chloromethyl)phenyl)‐4‐methylbenzenesulfonamide (aza‐ortho‐quinone methide precursor) under super basic conditions afforded hydrazine substituted sulfonamides.

  DOI：

  10.1002/ejoc.202400151

文献信息

• Visible-light-driven Cadogan reaction
  作者：Zhonghua Qu、Pu Wang、Xing Chen、Guo-Jun Deng、Huawen Huang

  DOI：10.1016/j.cclet.2021.02.047

  日期：2021.8

  endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

  已发现可见光驱动的光化学卡多根型环化。发现有机 DA 型光敏剂 4CzIPN 是将能量从光子转移到瞬态中间体的有效介质，该中间体打破了卡多根反应中的脱氧壁垒，并使无温和金属的咔唑和相关杂环成为可能。DFT 计算结果表明硝基双芳烃和 PPh 3的中间体复合物的温和吸能形成，这与关于反应温度的实验结果一致。光氧化还原 Cadogan 反应系统的强大合成能力已通过广泛范围的咔唑和相关N-杂环的可行生产力得到证明，这些N-杂环对各种官能团具有良好的耐受性。
• Rhodium(III)-Catalyzed Azidation and Nitration of Arenes by CH Activation
  作者：Fang Xie、Zisong Qi、Xingwei Li

  DOI：10.1002/anie.201305902

  日期：2013.11.4

  nitrite served as readily available nitrogen sources, and pyridine, pyrimidine, and pyrazole substituents were efficient directing groups (DGs; see scheme; Cp*=C5Me5). The synthetic utility of the azidation products was demonstrated in subsequent functional‐group transformations.

  掌握解决方案：在存在高价碘氧化剂的螯合辅助标题反应中，叠氮化钠和亚硝酸钠是易于获得的氮源，吡啶，嘧啶和吡唑取代基是有效的导向基团（DG；参见方案； Cp * = C 5 Me 5）。叠氮化产物的综合效用在随后的功能组转化中得到了证明。
• A concise Friedländer/Buchwald–Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline
  作者：María V. Méndez、Sebastian O. Simonetti、Teodoro S. Kaufman、Andrea B. J. Bracca

  DOI：10.1039/c9nj01961h

  日期：——

  A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedländer condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald–Hartwig

  据报道，有一种新的合成喹啉的方法，喹啉是一种公认​​的吲哚喹啉生物碱。该序列包括通过优化2-氨基苯甲醛与2-硝基苯乙酮的弗里德兰德缩合反应合成2-（2-硝基苯基）喹啉，然后对喹啉部分进行选择性C-3溴化，以指导环化反应，还原硝基组和最后的布赫瓦尔德-哈特维格环化反应。另外，在DBU促进下，通过与碳酸二甲酯反应，喹啉也被转化为非天然的10-甲基喹啉。发现2-（2-硝基苯基）喹啉的非定向还原环化导致吲哚并[2,3- a]喹啉，而不是产生喹啉。DFT计算被用来解释这种反应的结果。这一发现表明，应该修改先前报道的喹啉的总合成结果。
• Limitations of the ‘Two-Phase’ Doebner-Miller Reaction for the Synthesis of Quinolines
  作者：Wendy Loughlin、Kristie Reynolds、David Young

  DOI：10.1055/s-0030-1258258

  日期：2010.11

  The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only

  研究了修饰的双相条件下喹啉的Doebner-Miller合成。巴豆醛容易与苯胺反应生成2-甲基喹啉。但是，肉桂醛和其他γ-取代的α，β-不饱和醛会生成带有取代苯胺的复杂混合物，仅提供痕量的喹啉。在这些条件下的Doebner-Miller反应仅适用于空间可及的α，β-不饱和醛。 α，β-不饱和醛-苯胺-喹啉-Doebner-Miller反应-杂环
• 2-Arylquinolines and process for producing the same
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0786460A2

  公开（公告）日：1997-07-30

  2-Arylquinolines represented by formula (1): wherein R1, R3 to R9 each represents hydrogen, halogen, lower alkyl, cyclic lower alkyl, aryl, aralkyl, alkoxy or -CmF2m+1; R2 represents hydrogen, halogen, lower alkyl, cyclic lower alkyl, aryl, aralkyl, alkoxy, CnF2n+1 or -CH2Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having -NH- the hydrogen atom bonded to the nitrogen, or halogen; X represents halogen or hydrogen; Y represents nitro or amino which may be protected with a protecting group; and m and n each represents an integer of from 1 to 6; and processes for producing the 2-arylquinolines.

  由式(1)代表的 2-芳基喹啉： 其中 R1、R3 至 R9 各自代表氢、卤素、低级烷基、环状低级烷基、芳基、芳烷基、烷氧基或 -CmF2m+1；R2 代表氢、卤素、低级烷基、环状低级烷基、芳基、芳烷基、烷氧基、CnF2n+1 或 -CH2Q，其中 Q 代表从具有 -NH- 的有机化合物中除去与氮结合的氢原子或卤素而得到的一价有机基团； X代表卤素或氢；Y代表硝基或氨基，可被保护基团保护；m和n各代表1至6的整数；以及生产2-芳基喹啉的工艺。